1. Field of the Invention
The present invention relates to a novel process for producing .omega.-alkene-1-ols.
2. Description of the Prior Art
Heretofore, a process for producing olefins by dehydrating primary alcohols having one hydroxyl group using an acidic or basic material as the catalyst has been known. However, this dehydration reaction is often accompanied by ether formation due to intermolecular dehydration, and by double bond transfer in the dehydrated products (Eugen Muller, Methoden der Organischen Chemie, Bd V/lb, 45 (1972)). Moreover, when this process is applied to .alpha.,.omega.-alkanediols having two hydroxyl groups, large amounts of various diolefins, various alkene-1-ols and polyethers are formed, which not only gives a far smaller yield of the desired product, .omega.-alkene-1-ol, but also makes it extremely difficult to isolate and purify the .omega.-alkene-1-ol from the resulting reaction mixture by conventional distillation.
A process for producing olefins by thermally decomposing acetates of primary alcohols (ibid, Bd V/lb, 105 (1972)) has also been known. In this process, although double bond transfer does not take place, the process requires two steps because the acetates must be prepared beforehand and separated prior to thermal decomposition and thus is complicated. In addition, in the production of .omega.-alkene-1-ols using this process, another disadvantage is that when the starting material, monoacetate of an .alpha.,.omega.-alkanediol, is produced it is difficult to obtain alone at a good yield because the .alpha.,.omega.-diacetate is produced as a by-product. Further, the acetic acid produced by the thermal decomposition undergoes decomposition to make its recovery difficult. Therefore, this process is not suitable for commercial purposes.
On the other hand, it is known that the direct dehydration of alkane-1,4-diols produces tetrahydrofuran derivatives by the intramolecular dehydration (Journal of Organic Chemistry, Vol. 32, 3650 (1967)).